4-methyl-3-tosyl-3,4-dihydro-[1,2,3]triazolo[4,5-b]indole | 1562569-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-3-tosyl-3,4-dihydro-[1,2,3]triazolo[4,5-b]indole
• 英文别名: 4-Methyl-3-(4-methylphenyl)sulfonyltriazolo[4,5-b]indole；4-methyl-3-(4-methylphenyl)sulfonyltriazolo[4,5-b]indole
• CAS: 1562569-28-1
• 化学式: C₁₆H₁₄N₄O₂S
• 分子量: 326.379
• InChiKey: IEVPBVQTJIUSPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-3-tosyl-3,4-dihydro-[1,2,3]triazolo[4,5-b]indole 、 茚 在 辛酸铑 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以97%的产率得到4-methyl-N-(1'-methyl-1a,6a-dihydro-6H-spiro[(trans)-cyclopropa[a]indene-1,3'-indolin]-2'-ylidene)benzenesulfonamide
  参考文献：
  名称：

  Preparation of Triazoloindoles via Tandem Copper Catalysis and Their Utility as α-Imino Rhodium Carbene Precursors

  摘要：

  3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as a-imino rhodium carbene precursors for the construction of a range of valuable indole molecules including pyrrolo[2,3-b] indoles, spirocyclopropyl iminoindoles, 2,3-dihydropyrrolo[2,3-b]indoles, 3,3'-biindoles, and 2,3'-biindoles.

  DOI：

  10.1021/ol5002347
• 作为产物：
  描述：

  对甲苯磺酰氯 在 sodium azide 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 4-methyl-3-tosyl-3,4-dihydro-[1,2,3]triazolo[4,5-b]indole
  参考文献：
  名称：

  Preparation of Triazoloindoles via Tandem Copper Catalysis and Their Utility as α-Imino Rhodium Carbene Precursors

  摘要：

  3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as a-imino rhodium carbene precursors for the construction of a range of valuable indole molecules including pyrrolo[2,3-b] indoles, spirocyclopropyl iminoindoles, 2,3-dihydropyrrolo[2,3-b]indoles, 3,3'-biindoles, and 2,3'-biindoles.

  DOI：

  10.1021/ol5002347

文献信息

• Engineering Chemoselectivity in Hemoprotein-Catalyzed Indole Amidation
  作者：Oliver F. Brandenberg、David C. Miller、Ulrich Markel、Anissa Ouald Chaib、Frances H. Arnold

  DOI：10.1021/acscatal.9b02508

  日期：2019.9.6

  providing the desired indole amidation products with up to 8400 turnovers, 90% yield, and a shift in chemoselectivity from 2:19:1 to 110:12:1 in favor of nitrene transfer over reduction or triazole formation. This work expands the substrate scope of hemoprotein nitrene transferases to heterocycles and highlights the adaptability of the P450 scaffold to solve challenging chemoselectivity problems in non-natural

  在这里，我们报告了一种细胞色素P450变体，它通过甲苯转移催化甲苯磺酰基叠氮化物催化1-甲基吲哚的C2酰胺化。在进化优化之前，该酶表现出两个不希望的副反应性，从而导致推定的铁-类氮烯中间体或两个底物之间的环加成反应减少，从而形成三唑产物。我们推测三唑的形成是P450血红素结构域的混杂环加成活性，而磺酰胺的形成可能是由于还原酶结构域中多余的电子转移引起的。涉及血红素和还原酶结构域诱变的定向进化提供了一种酶，该酶提供了所需的吲哚酰胺化产物，其转化率高达8400，产率为90％，化学选择性从2：19：1变为110：12：1有利于氮的转移而不是还原或三唑的形成。这项工作将血红蛋白氮转移酶的底物范围扩大到了杂环，并强调了P450支架在解决非天然酶催化中具有挑战性的化学选择性问题方面的适应性。
• Preparation of Triazoloindoles via Tandem Copper Catalysis and Their Utility as α-Imino Rhodium Carbene Precursors
  作者：Yanpeng Xing、Guorong Sheng、Jing Wang、Ping Lu、Yanguang Wang

  DOI：10.1021/ol5002347

  日期：2014.2.21

  3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as a-imino rhodium carbene precursors for the construction of a range of valuable indole molecules including pyrrolo[2,3-b] indoles, spirocyclopropyl iminoindoles, 2,3-dihydropyrrolo[2,3-b]indoles, 3,3'-biindoles, and 2,3'-biindoles.